60282-87-3
60282-87-3
Chemical Structure
Gestodene
Synonym(s): SHB 331; WL 70
- CAS No.: 60282-87-3
- Formula:C21H26O2
- Molecular Weight:310.43
IUPAC Name: (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
InChIKey: SIGSPDASOTUPFS-XUDSTZEESA-N
SMILES: CC[C@@]1([C@]2(O)C#C)[C@](C=C2)([H])[C@@](CCC3=CC4=O)([H])[C@]([C@@]3([H])CC4)([H])CC1
Biological Activity: Gestodene (SHB 331; WL 70) is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis[1][2][3][4][5][6][7][8].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Gestodene | 99.89% | Gestodene (SHB 331; WL 70) is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis. | ||||||||||||||||||||
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Gestodene (Standard) | ≥98% | Gestodene (Standard) (SHB 331 (Standard); WL 70 (Standard)) is the analytical standard of Gestodene (HY-B0110). This product is intended for research and analytical applications. Gestodene is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis. | ||||||||||||||||||||
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Gestodene-d7 | Gestodene-d7 (SHB 331-d7; WL 70-d7) is the deuterated-labeled Gestodene (HY-B0110). Gestodene is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis. | |||||||||||||||||||||
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Gestodene-d6 | Gestodene-d6 (SHB 331-d6; WL 70-d6) is the deuterated-labeled Gestodene (HY-B0110). Gestodene is an orally active synthetic progestogen compound of the 19-nortestosterone class. Gestodene binds with high affinity to the progesterone receptor, inhibits 5α-reductase, binds to androgen and aldosterone receptors, and inactivates CYP3A. Gestodene acts as a positive allosteric modulator of PAR1, enhances PAR1-mediated signaling pathways, and is capable of increasing the activation potency of PAR1-AP toward PAR1, thereby promoting ERK1/2 phosphorylation, receptor internalization, cell morphological changes, and human platelet aggregation. Gestodene and its A-ring reduced metabolites promote the proliferation, differentiation, and mineralization of neonatal rat osteoblasts. Gestodene itself has no binding capacity for estrogen receptors, and this osteogenic activity depends on intracellular metabolism to generate A-ring reduced products with estrogen-like agonistic activity. Gestodene is useful for research on diseases related to progesterone secretion and diseases related to thrombosis. | |||||||||||||||||||||
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References
- [1]. Stanczyk FZ, et al. Gestodene: a review of its pharmacology, potency and tolerability in combined contraceptive preparations. Contraception. 2014 Apr;89(4):242-52.
- [2]. Enríquez J, et al. The synthetic progestin, gestodene, affects functional biomarkers in neonatal rat osteoblasts through an estrogen receptor-related mechanism of action. Endocrine research. 2017 Nov;42(4):269-280.
- [3]. Lemus AE, et al. In vitro metabolism of gestodene in target organs: formation of A-ring reduced derivatives with oestrogenic activity. European journal of pharmacology. 2001 Apr 13;417(3):249-56.
- [4]. Jeon H, et al. Gestodene Accelerates Cutaneous Wound Healing via PAR1-Selective Positive Allosteric Modulation. International journal of molecular sciences. 2026 Jun 18;27(12):5502.
- [5]. Park SH, et al. Gestodene, a novel positive allosteric modulator of PAR1, enhances PAR1-mediated human platelet aggregation. Frontiers in pharmacology. 2024;15:1430548.
- [6]. Pech M, et al. Effect of gestodene on the reproduction of zebrafish (Danio rerio). Environmental toxicology and pharmacology. 2026 Aug;125:105070.
- [7]. Schoonen WG, et al. Effects of two classes of progestagens, pregnane and 19-nortestosterone derivatives, on cell growth of human breast tumor cells: II. T47D cell lines. The Journal of steroid biochemistry and molecular biology. 1995 Dec;55(3-4):439-44. [Content Brief]
- [8]. Enríquez J, et al. The potent contraceptive gestodene exerts insulinotropic effects through its a-ring reduced metabolites with intrinsic estrogen-like activity in pancreatic β-cells. Journal of endocrinological investigation. 2023 Jul;46(7):1333-1341.
